| 1 | Reynolds Rappaport & Kaplan | €12.2M | 30 | 60 | C+ |
| 2 | Bear Baby Equipment Rentals | €12.2M | 30 | 60 | C+ |
| 3 | Chappaquiddick Beach Club Inc | €8.5M | 30 | 50 | C |
| 4 | granite ace hardware distribution warehouse | €7.8M | 30 | 50 | C |
| 5 | Callen Maritime Group | €6.8M | 5 | 50 | C |
| 6 | Herring Creek Marine Inc | €6.8M | 5 | 50 | C |
| 7 | OnislandMV™ | €6.6M | 30 | 50 | C |
| 8 | Berube Electric Inc | €5.9M | 30 | 50 | C |
| 9 | kelley house hotel | €5.1M | 125 | 50 | C |
| 10 | the boathouse & field club | €5.1M | 125 | 50 | C |
| 11 | Lightkeepers Inn | €4.9M | 30 | 50 | C |
| 12 | Harborside Inn Resort | €4.9M | 30 | 50 | C |
| 13 | Martha’s Vineyard Transit Authority | €4.9M | 30 | 50 | C |
| 14 | Vineyard Square Hotel & Suites | €4.9M | 30 | 50 | C |
| 15 | Landscope Inc. | €4.5M | 30 | 50 | C |
| 16 | Island Home Services | €4.5M | 30 | 50 | C |
| 17 | larry’s tackle shop | €4.1M | 30 | 50 | C |
| 18 | Big Sky Tent & Party Rentals | €3.3M | 30 | 50 | C |
| 19 | Edgartown Police Dept | €3.0M | 30 | 50 | C |
| 20 | Backwater Trading Company | €3.0M | 30 | 50 | C |
| 21 | AAC Consulting | €2.8M | 30 | 50 | C |
| 22 | edgartown, town of | €2.8M | 30 | 50 | C |
| 23 | aac consulting, inc. | €2.1M | 30 | 50 | C |
| 24 | vineyard bath | €2.1M | 5 | 50 | C |
| 25 | Shiretown Meats | €2.0M | 5 | 50 | C |
| 26 | Edgartown Paint Stop | €2.0M | 5 | 50 | C |
| 27 | martha’s vineyard gourmet cafe’& bakery | €2.0M | 5 | 50 | C |
| 28 | Point B | Compass | €2.0M | 30 | 50 | C |
| 29 | carroll and vincent | €2.0M | 30 | 50 | C |
| 30 | Carroll and Vincent Real Estate | €2.0M | 30 | 50 | C |
| 31 | Wallace & Co. Sotheby's International Realty, Martha's Vineyard Real Estate | €2.0M | 30 | 50 | C |
| 32 | Accurate Cab | €1.4M | 5 | 50 | C |
| 33 | BIODIVERSITYWORKS INC | €1.4M | 5 | 50 | C |
| 34 | Island Source | €1.2M | 5 | 50 | C |
| 35 | Epicure MV | €1.2M | 5 | 50 | C |
| 36 | the newes from america pub | €1.2M | 30 | 50 | C |
| 37 | al’s package store | €1.2M | 30 | 50 | C |
| 38 | david ryan’s restaurant & cafe | €1.2M | 30 | 50 | C |
| 39 | Alchemy Bistro & Bar | €1.2M | 30 | 50 | C |
| 40 | chesca’s restaurant | €1.2M | 30 | 50 | C |
| 41 | Chappy Chips | €995K | 5 | 40 | D |
| 42 | MarTech Conference | €908K | 30 | 40 | D |
| 43 | navigator homes of martha's vineyard | €834K | 5 | 40 | D |
| 44 | island hearing services llc | €834K | 5 | 40 | D |
| 45 | Cuttyhunk Fishing Club Bed & Breakfast | €821K | 5 | 40 | D |
| 46 | Harborside Triangle Liquors | €816K | 2 | 40 | D |
| 47 | Baumhofer Builders Inc | €811K | 5 | 40 | D |
| 48 | Edgartown Paper Store | €811K | 5 | 40 | D |
| 49 | Marthas Vineyard Construction Co. Inc. | €755K | 5 | 40 | D |
| 50 | Rosbeck Builders | €755K | 5 | 40 | D |
| 51 | edgartown water dept | €755K | 5 | 40 | D |
| 52 | rick convery painting & rstrtn | €755K | 5 | 40 | D |
| 53 | Bettencourt Irrigation Systems | €755K | 5 | 40 | D |
| 54 | industrious builders, inc | €755K | 5 | 40 | D |
| 55 | foggy bottom company llc | €755K | 5 | 40 | D |
| 56 | vineyard propane & oil | €641K | 5 | 40 | D |
| 57 | contour landscape construction | €641K | 5 | 40 | D |
| 58 | Chappaquiddick Community Ctr | €627K | 5 | 40 | D |
| 59 | Singular Spaces | €627K | 5 | 40 | D |
| 60 | Vineyard Hearth Patio & Spa | €612K | 5 | 40 | D |
| 61 | Mattakesett Properties | €572K | 5 | 40 | D |
| 62 | green squirrel landscaping & construction | €545K | 30 | 40 | D |
| 63 | scrubcuts | €545K | 30 | 40 | D |
| 64 | working earth gardening | €512K | 5 | 40 | D |
| 65 | Edgartown Highway Dept | €503K | 5 | 40 | D |
| 66 | Swell Affair | €495K | 5 | 40 | D |
| 67 | edgar mv | €465K | 5 | 40 | D |
| 68 | debra m gaines fine art gallery | €465K | 5 | 40 | D |
| 69 | Edgartown Council On Aging | €429K | 5 | 40 | D |
| 70 | Mad Martha's | €372K | 5 | 40 | D |
| 71 | swift house cleaning | €372K | 5 | 40 | D |
| 72 | Richard Hamilton, Goldsmith | €372K | 2 | 40 | D |
| 73 | Kevin Butler Gallery | €331K | 5 | 40 | D |
| 74 | Jon Ashton Enterprises | €331K | 5 | 40 | D |
| 75 | Detrick Lawrence Corp | €331K | 5 | 40 | D |
| 76 | deepwater estate services | €328K | 5 | 40 | D |
| 77 | Ledden Properties | €328K | 5 | 40 | D |
| 78 | Great Harbor Real Estate | €328K | 5 | 40 | D |
| 79 | Cape Real Estate Software | €328K | 5 | 40 | D |
| 80 | Priestley Smadbeck & Mone | €328K | 5 | 40 | D |
| 81 | Edgartown Inn | €328K | 5 | 40 | D |
| 82 | hob knob realty | €328K | 5 | 40 | D |
| 83 | designs gallery | €328K | 5 | 40 | D |
| 84 | katama realty group | €328K | 5 | 40 | D |
| 85 | gentle’s realty | €328K | 5 | 40 | D |
| 86 | viglas property management | €328K | 5 | 40 | D |
| 87 | Seacoast Properties | €328K | 5 | 40 | D |
| 88 | Walter Smith Plumbing & Htg | €311K | 5 | 40 | D |
| 89 | marthas vineyard striped bass and bluefish derby inc | €283K | 5 | 40 | D |
| 90 | MARTHAS VINEYARD BOYS & GIRLS CLUB | €269K | 30 | 40 | D |
| 91 | Edgartown Free Public Library | €268K | 5 | 40 | D |
| 92 | REYNOLDS, RAPPAPORT, KAPLAN & HACKNEY, LLC | €267K | 30 | 40 | D |
| 93 | Edgartown Lodge | €253K | 5 | 40 | D |
| 94 | lattanzis restaurant | €204K | 5 | 40 | D |
| 95 | marthas vineyard law enforcement council inc | €204K | 5 | 40 | D |
| 96 | allanbrook business svc | €183K | 5 | 40 | D |
| 97 | CR Growth Solutions | €136K | 5 | 40 | D |
| 98 | Fresh Pasta Shoppe | €127K | 1 | 40 | D |
| 99 | Shored Up Digital | €108K | 5 | 40 | D |
| 100 | wheel happy too | €105K | 5 | 40 | D |